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IT Senior Program Manager

Paradigm

Paradigm

IT, Operations
Lombard, IL, USA
Posted on Mar 6, 2026

We are seeking a full-time, remote IT Program Manager. The IT Program Manager will be responsible for leading and developing a team of project managers, establishing clear roles and processes, and ensuring disciplined delivery of complex, cross-functional programs. They play a key role in shaping Paradigm’s project management framework, driving strategic direction, and fostering a culture of accountability, innovation, and continuous improvement.

RESPONSIBILITIES:

Strategic Direction & Role Clarity

  • Define, communicate, and enforce clear roles and responsibilities for project managers, supporting Paradigm’s transition to a structured, process-driven framework.
  • Mentor, train, and supervise project managers, providing effective feedback and fostering a high-performance team culture.
  • Guide, maintain, and enforce departmental practices, methodologies, policies, and procedures.

Scope Management & Timeboxed Releases

  • Lead the team in planning high-level features and scope items for timeboxed releases, ensuring incremental and predictable delivery.
  • Coordinate with internal stakeholders to understand business goals and objectives, translating them into actionable directives for project managers interacting with digital product teams and business analysts.
  • Maintain situational awareness and a keen sense of urgency in responding to digital product, business, and IT environmental influences.

Governance, Reporting & Resource Management

  • Implement robust governance standards, including RAID logs, risk management, and mitigation planning.
  • Oversee status tracking, resource prioritization, and schedule adherence for all programs.
  • Establish and track IT implementation metrics (KPIs) and team dashboards to increase visibility, alignment, and accountability.
  • Produce regular, comprehensive reporting on project/program status, budgets, schedules, resource allocation, and operational effectiveness for the Steering Committee and leadership team.

Quality Assurance & Deployment Discipline

  • Champion disciplined QA/UAT and deployment processes, ensuring accuracy in project management tools and timely communication of deployment readiness.
  • Support the team in developing and maintaining project milestones, work breakdown structures, and contingency plans.
  • Ensure successful implementation within defined timeframes and budgets.

Innovation & AI Enablement

  • Drive adoption of AI tools (e.g., Microsoft 365 Copilot) to enhance project management efficiency, automate status summaries, risk registers, and weekly updates.
  • Work with App Dev Directors and digital product owners on continuous improvements of technology capabilities to ensure efficient and effective implementations.
  • Provide strategic insights to organizational leaders on process improvements that reduce time to market, lower costs, and increase ROI.

Stakeholder Engagement & Communication

  • Maintain communication with digital product management and internal stakeholders on overall project status, milestones, and risks.
  • Create and maintain standard operating process reference material for internal staff and digital product management, including workflows and solution delivery protocols.
  • Demonstrate outstanding communication and presentation skills, conveying sophisticated concepts simply and clearly to a variety of audiences.

SUPERVISORY RESPONSIBILITIES:

  • Mentor, train, and supervise team members directly and indirectly, review their work and provide effective constructive feedback to achieve their best performance and goal attainment
  • Set the tone for a strong Enterprise culture and high employee engagement.
  • Ensure all team members understand, are trained in, and comply with Paradigm’s security requirements and policies.
  • Ensure all team members have the minimum level of IT system access required to effectively complete their Paradigm responsibilities.

QUALIFICATIONS:

  • Bachelor’s Degree in Computer Science, Project Management, Business Management, or related field, or equivalent experience.
  • 8-10 years of program/portfolio planning and management experience.
  • 15+ years of direct IT project management experience, including managing multiple projects and leading project managers.
  • PMP or PMP-ACP certification required.
  • Demonstrated experience leading strategic technology initiatives.
  • Proven expertise in project governance, risk management, change management, and people management.
  • Strong business/digital product management engagement, communication, and organizational skills.
  • High proficiency with project management tools (e.g., MS Project, Planview), Microsoft productivity tools, and MS Office suite.
  • Strong business analysis and IT integration skills.
  • Strong IT Agile experience.
  • Working knowledge of the Workers’ Comp industry is a plus.

What We Value

  • Defined PM roles and structured governance.
  • Clear scope for timeboxed releases.
  • Comprehensive reporting (RAID, risk, financial health).
  • Disciplined QA/UAT and deployment processes.
  • Adoption of AI tools for PM efficiency.